Author: Jessica.F

Application of 5394-18-3,Some common heterocyclic compound, 5394-18-3, name is 2-(4-Bromobutyl)isoindoline-1,3-dione, molecular formula is C12H12BrNO2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

N-(4-Bromobutyl)phthalimide (1.5 g, 5.32 mmol) was suspendedin THF (48 mL) and treated with sodium iodide (0.80 g, 5.32 mmol), triethylamine (0.74 mL, 5.32 mmol) and morpholine (0.51 mL, 5.85 mmol). The mixture was then heated at reflux for 16 h. After cooling to ambient temperature, the solvent was removed in vacuo and the residue partitioned between H2O (100 mL) and CHCl3 (100 mL). The aqueous layer was further extracted with CHCl3 (100 mL) and the organic extracts combined, dried (MgSO4), filtered, filtered and the solvent removed under reduced pressure. The crude product was purified by flash chromatography on silica eluting with ethyl acetate to give phthalimide10 (1.02 g, 66%) as a pale yellow oil; numax/cm-12942, 2855, 2807, 1703, 1393, 1359, 1333, 1114, 1069, 1011, 862, 716, 528; deltaH (300 MHz; CDCl3) 7.86-7.77 (2 H, m), 7.73-7.67 (2 H, m), 3.69 (6 H, m), 2.40 (6 H, m), 1.71 (2 H, m), 1.50 (2 H, m); deltaC (75 MHz; CDCl3) 168.5, 134.0, 132.2, 123.3, 66.9, 58.4, 53.7, 37.9, 26.6, 23.8; m/z (+ESI) 289 ([M + H]+, 100); Found: M+, 289.15493. C16H20N2O3 requires 289.15467.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromobutyl)isoindoline-1,3-dione, its application will become more common.

Reference:
Article; Beinat, Corinne; Reekie, Tristan; Hibbs, David; Xie, Teresa; Olson, Thao T.; Xiao, Yingxian; Harvey, Andrew; O’Connor, Susan; Coles, Carolyn; Tsanaktsidis, John; Kassiou, Michael; European Journal of Medicinal Chemistry; vol. 84; (2014); p. 200 – 205;,
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Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 22190-33-6, name is 5-Bromoindoline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H8BrN

A solution of 5-bromo-2,3-dihydro-1H-indole (4.97 g, 25.1 mmol), di-tert-butyl dicarbonate (6.0 g, 27.5 mmol) and 4-dimethylaminopyridine (catalytic) in dichloromethane (70 mL) was stirred at room temperature until the starting material was consumed. The solvent was evaporated in vacuo, and the residue was purified by flash chromatography on silica gel, eluted with ethyl acetate/hexane to give the product, 4.1 g (55%). 1H NMR (CDCI3) : delta 1.55 (s, 9 H), 3.06 (t, 2 H), 3.97 (t, 2 H), 7.23-7.27 (m, 2 H) and 7.72 (br m, 1 H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 22190-33-6.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2004/69792; (2004); A2;,
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Indoline | C8H9N – PubChem

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 20870-79-5, name is 5-Nitroindolin-2-one, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 20870-79-5

Preparation of 5-amino-oxindole (2) To a solution of 5-nitro-oxindole (25 g) in 120 mL of dimethylacetamide in a Parr bottle was added 10% Pd/C (0.5 g). The mixture was hydrogenated (40 psi H2) for 16 hours. The catalyst was removed by filtration and the filtrate was diluted with ether (2 L) to provide 5-amino-oxindole (10.5 g; 50%).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 20870-79-5.

Reference:
Patent; Pfizer Inc; US2005/256145; (2005); A1;,
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Related Products of 7147-90-2, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

3.6 g of 1,1, 1-trifluoro-3-iodopropane are added dropwise to a mixture of 7.5 g of 4- chlorophthalimide and 4.6 g of potassium carbonate in 40 cm3 of [DIMETHYLFORMAMIDE] at a temperature in the region of [110C] with stirring. After stirring for 11 hours at a temperature in the region of [120C,] the reaction mixture is cooled to a temperature in the region [OF 20C] and then poured into 200 cm3 of water. The mixture is acidified with dilute aqueous hydrochloric acid solution to a pH of about 3, and is then extracted 3 times with 100 cm3 of ethyl acetate. The organic phase is dried over magnesium sulphate and then concentrated to dryness. 5.0 g [OF 4-CHLORO-N- (3,] 3, 3-trifluoro- propyl) phthalamic acid are thus obtained, Rf = 0.12 (thin layer chromatography on silica gel, eluent : ethyl acetate)

The chemical industry reduces the impact on the environment during synthesis 5-Chloroisoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AVENTIS PHARMA DEUTSCHLAND GMBH; WO2003/101450; (2003); A1;,
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Application of 20870-90-0, A common heterocyclic compound, 20870-90-0, name is 5-Bromo-1-methyl-2-oxoindoline, molecular formula is C9H8BrNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

General procedure: To a Schlenk tube were added oxindole 1 (0.3 mmol), t-BuONO (0.6 mmol), andTHF (2 mL). Then the tube was stirred at 50 C under 1 atm of O2 for the indicatedtime until complete consumption of starting material monitored by TLC analysis.After the reaction was finished, the reaction mixture was washed with brine. The aqueous phase was re-extracted with ethyl acetate. The combined organic extractswere dried over Na2SO4, removal of the solvent under vacuum afforded the crudeproduct, which was purified further by column chromatography using hexane-ethylacetate.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Wei, Wen-Ting; Ying, Wei-Wei; Zhu, Wen-Ming; Wu, Yi; Huang, Yi-Ling; Cao, Yi-Qi; Wang, Yi-Ning; Liang, Hongze; Synlett; vol. 28; 17; (2017); p. 2307 – 2310;,
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Related Products of 7147-90-2, The chemical industry reduces the impact on the environment during synthesis 7147-90-2, name is 5-Chloroisoindoline-1,3-dione, I believe this compound will play a more active role in future production and life.

To a solution of 5-chloro-isoindole-l,3-dione (5.0 g, 27.5 mmol) in DCM (200 mL) was added ethylmagnesium chloride (2 M in THF, 41.3 mL) dropwise at 0 C. After the addition, the mixture was allowed to stir at 0 C for 3 hours before it was quenched with satd. aq. NH4C1 solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude product containing a mixture of two regioisomers (5.82 g, 100%). MS: 212.0 (M+H+).; Under N2 protection, triethylsilane (19.3 g, 166 mmol) and TFA (20 mL) were added successively to a mixture of 5-chloro-3-ethyl-3-hydroxy-2,3-dihydro-isoindol- 1 -one and 6- chloro-3-ethyl-3-hydroxy-2,3-dihydro-isoindol-l-one (3.52 g, 16.6 mmol). After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. The residue was treated with a satd. aq. solution of NaHCC>3 (30 mL) and extracted with DCM (2 x 30 mL). The combined organic layers were washed with brine, dried over anhy. Na2S04, filtered and concentrated in vacuo to give a crude mixture of products. Both 5-chloro-3-ethyl-2,3-dihydro-isoindol-l-one (0.65 g, 20%) MS: 196.1 – 147 -(M+H+) and 6-chloro-3-ethyl-2,3-dihydro-isoindol-l-one (0.62 g, 19%) MS: 196.1 (M+H+) were obtained by prep-HPLC separation as white solids.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 5-Chloroisoindoline-1,3-dione, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; AEBI, Johannes; AMREIN, Kurt; CHEN, Wenming; HORNSPERGER, Benoit; KUHN, Bernd; LIU, Yongfu; MAERKI, Hans P.; MAYWEG, Alexander V.; MOHR, Peter; TAN, Xuefei; WANG, Zhanguo; ZHOU, Mingwei; WO2013/79452; (2013); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 3485-84-5, name is N-Vinylphthalimide, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 3485-84-5, Safety of N-Vinylphthalimide

A thick walled glass tube, equipped with a stir bar, was charged with palladium (II) acetate (64 mg, 0.29 mmol), acetonitrile (50 mL), JV-vinylphthalimide (1.19 g, 6.89 mmol), triethylamine (2.4 mL, 17 mmol), tri-o-tolylphosphine (260 mg, 0.86 mmol) and l-(7-bromo-2-ethyl-17f-imidazo[4,5-c]quinolin-l-yl)-2-methylpropan-2-ol (2.00 g, 5.74 mmol). The reaction mixture was purged with nitrogen and the tube was sealed and heated at 120 0C in an oil bath for 16 hours. The reaction was cooled to ambient temperature and silica gel (20 g) was added followed by concentration under reduced pressure. The sample absorbed on silica was purified by chromatography using a HORIZON HPFC system (silica cartridge, eluting with a 0-7% gradient of methanol in dichloromethane). The recovered solid was washed with 1% aqueous sodium carbonate to provide 1.95 g of 2-{2- EPO [2-ethyl- 1 -(2-hydroxy-2-methylpropyl)- 1 H-imidazo[4,5 -c]quinolin-7-yl]ethenyl} – 1 H- isoindole-l,3(2H)-dione as a bright yellow solid. MS (APCI) m/z 441 (M + H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N-Vinylphthalimide, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; 3M INNOVATIVE PROPERTIES COMPANY; WO2006/91394; (2006); A2;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

Adding a certain compound to certain chemical reactions, such as: 893620-44-5, name is 6-Bromo-5-fluoroindolin-2-one, belongs to indolines-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 893620-44-5, COA of Formula: C8H5BrFNO

d) 6-Bromo-5-fluoro-1 ,3-trimethylindolin-2-one To a suspension of NaH (5.04 g, 126 mmol) in tetrahydrofuran (105 ml) under an argon atmosphere was added 6-bromo-5-fluoroindolin-2-one (7.24 g, 31.5 mmol) in portions. After gas evolution has ceased methyl iodide (17.9 g, 7.88 ml, 126 mmol) was added dropwise within 50 minutes by means of a syringe pump (exothermic reaction), keeping the temperature of the reaction mixture between 24C and 26C. The reaction mixture was kept at room temperature for 4 hours and then carefully quenched with aqueous ammonium chloride solution. The reaction mixture was diluted with tert-butyl methyl ether, water and saturated aqueous ammonium chloride solution. The aqueous phase was extracted with tert-butyl methyl ether, the combined organic phases were washed with saturated aqueous ammonium chloride and dried over sodium sulfate. The solvent was evaporated and the residue was triturated with heptane to give the title compound as light brown solid (7.87 g). 1H NMR (CDC13, 400 MHz): (ppm) = 7.02-6.97 (m, 2H), 3.19 (s, 3H), 1.36 (s, 6H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Bromo-5-fluoroindolin-2-one, and friends who are interested can also refer to it.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; BRUNNER, Daniela; MALBERG, Jessica; SHANKAR, Bavani G.; KOLCZEWSKI, Sabine; LIMBERG, Anja; PRINSSEN, Eric; RIEMER, Claus; STOLL, Theodor; WO2014/40969; (2014); A1;,
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Indoline | C8H9N – PubChem

Electric Literature of 1074-82-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1074-82-4 as follows.

To a solution of 1 -bromo-4-bromomethyl-benzene (3.0 g, 12.0 mmol, 1.0 eq) in DMF (40 mL) was added phthalimide potassium (4.4 g, 24.0 mmol, 2.0 eq). The reaction mixture was stirred for 1 h at rt Water was added, and the mixture was extracted with EtOAc. The organic layer was dried over Na2S04 and evaporated to give 2-(4-bromo-benzyl)-isoindole-l,3-dione which was used as a white solid (4.0 g, quant)without further purification.

According to the analysis of related databases, 1074-82-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LIFESCI PHARMACEUTICALS, INC.; MCDONALD, Andrew; WO2015/103317; (2015); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem

In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 118289-55-7 as follows. Recommanded Product: 118289-55-7

88.7 g (0.837 mols, 3.21 molar equivalents) of sodium carbonate, 600 mL of acetonitrile and 66.7 g (0.261 mols, 1.0 molar equivalent) of 3- (1-piperazinyl) -1, 2- benzisothiazole hydrochloride are added into a beaker equipped with a magnetic stirrer. The resulting white suspension is stirred for 10 minutes. At this point 60.0 g (0.261 mols, 1.0 molar equivalent) of 5- (2- chloroethyl) -6-chloro-l, 3-dihydro-indole-2- (2H) -one and 0.3 g (0.002 mols, 0.008 molar equivalents) of NaI are added. The resulting brown suspension is charged into a 1 L reactor vessel, which is purged with nitrogen and heated to 120-125 C (internal pressure increases to 400- 500 kPa) for 25 hours. The reaction is cooled to room temperature, stirred for 30 minutes, filtered and the solid washed with acetonitrile. A wet mixture of zipradisone and inorganic salts is obtained, that is further washed with acetonitrile. The resulting wet mixture of ziprasidone and inorganic salts is stirred with 675 ml of water at reflux temperature for 1 h to remove inorganic salts. The suspension is cooled to room temperature, stirred for 30 minutes and filtered. The solid is washed with water, and 140 g of wet solid (corresponding to 87 g of dry material) are obtained. EPO The wet solid is stirred again with water at reflux temperature for 1 h to remove residual inorganic salts. The suspension is cooled to room temperature, stirred for 30 minutes and filtered. The solid is washed with water, and 170 g of wet solid (corresponding to 81 g of dry- material) are obtained. HPLC analysis reveals a purity of 97.8%.To remove starting materials present in the wet solid obtained in the previous step, it is stirred twice with400 ml of tetrahydrofuran at reflux temperature. The solution is cooled to room temperature, stirred for 30 minutes and filtered. The solid is washed twice with 40 ml of tetrahydrofuran, and 60 g of wet solid, corresponding to 54.8 g of dry material, are obtained.The solid obtained is ziprasidone base having a purity of 99.4% by HPLC and the global yield from the starting compounds is 51% (molar yield) . Potentiometric titration with HClO4: 100.03%

According to the analysis of related databases, 118289-55-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MEDICHEM, S.A.; WO2006/34965; (2006); A1;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem